While the dough chills, I make the simple strawberry cream cheese filling. In a small bowl, I beat the remaining 4 ounces of softened cream cheese with the powdered sugar and teaspoon of vanilla until smooth. In another small bowl, I have my strawberry jam ready. Once the dough is chilled, I scoop it: I use a tablespoon-sized cookie scoop to form balls, placing them about 2 inches apart on the prepared baking sheets. Then, I use the back of a small spoon or my thumb to make a deep, wide well in the center of each dough ball.
Here’s the fun part: assembly. I place about ½ teaspoon of the sweetened cream cheese mixture into each well. Then, I top that with about ½ teaspoon of the strawberry jam, letting it sit right on the cream cheese. I don’t swirl them together; I like the distinct layers. The dough may crack a little, which is fine. Sometimes, I’ll sprinkle a pinch of crushed freeze-dried strawberry over the top for extra flavor and a pretty look. I bake the cookies for 11-13 minutes, just until the edges are set and very lightly golden. The centers will look soft—that’s what you want! I let them cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely. The filling sets as they cool.
Pro Tips for Best Results
I’ve tested the dough chilling three different ways: no chill, 30 minutes, and overnight. Thirty minutes is the sweet spot. No chilling led to flat, greasy cookies that spread into each other. Overnight made the dough too firm and dense. That half-hour chill firms up the fats just enough to give you a cookie that holds its shape but still bakes up soft and tender.
Here’s what I learned the hard way about the fillings: ensure your cream cheese is truly softened for both the dough and the filling. Cold cream cheese will create lumps in the dough and a lumpy filling. I take mine out of the fridge at least an hour before I start. If I’m short on time, I cut it into cubes and let it sit on the counter for 20 minutes. Smooth ingredients are the secret to perfect cookies.
For the jam, I sometimes warm it slightly for 10 seconds in the microwave. This makes it easier to spoon and creates a beautiful, glossy finish as it bakes. Just don’t make it hot, or it will start to melt the cream cheese filling. A quick warm-up is the trick to a pretty, shiny strawberry center.
Common Mistakes to Avoid
My biggest first-time mistake was over-filling the wells. I got excited and piled in both fillings, thinking more was better. During baking, the fillings bubbled over the sides, ran onto the pan, and made a sticky mess. The cookies stuck, and the presentation was ruined. A scant half-teaspoon of each filling is plenty—it bakes into a perfect, contained little pocket.
Another error is not softening the butter and cream cheese adequately. I was impatient once and tried to mix with cool ingredients. The sugars never fully incorporated, leaving a grainy texture, and the dough was uneven. The result was cookies with a strange, greasy film. Taking the time to get them to true room temperature is a non-negotiable step for a smooth dough and perfect texture.(See the next page below to continue…)